Benzoyl Peroxide → HCID 54452167, compound

HRID 1587573Notes

Reaction equation

HRID 1587573 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[C:5]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)=[O:6].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Br:36]Br>C(Br)CBr>[Br:36][CH2:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[C:5]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)=[O:6]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 24408BromineHCID 12469466(4-Methoxyphenyl)(3-methylphenyl)methanone

Product 1

HCID 54452167HCID 54452167, compoundYield 60.8%

Reagents, catalysts & solvents 1

HCID 78391,2-DibromoethaneSolvent2×

Procedure

A solution of the benzophenone (17.5 g, 77.4 mmole) of Step A in ethylene bromide (26.5 mL) (containing a small amount of benzoyl peroxide) is heated at reflux. A solution of bromine (12.7 g, 79.6 mmole) in ethylene bromide (15 mL) is added dropwise over 30 minutes while the mixture is irradiated with a Photolamp (300 W). Reflux is continued for 17 hours (TLC, 9:1 petrolether-ethylacetate, traces of starting material still present). The solvent is removed in vacuo and the residue (brown oil, 39.22 g) is purified by flash chromatography (on silica Merck-60, preabsorbed in dichloromethane, eluted with 9:1 petrolether-ethyl acetate) to give unreacted starting material (2.59 g, ca. 15%) along with the desired product (14.36 g, 61% or 71.5% based on recovered unreacted starting material) and some mixed fraction (ca. 5.20 g). The light yellow solid melts at 58°-61° C. and it is used as such in the next step.

Workup

  1. temperatureis heated
  2. temperatureat reflux
  3. customis irradiated with a Photolamp (300 W)
  4. temperatureReflux
  5. customThe solvent is removed in vacuo
  6. customthe residue (brown oil, 39.22 g) is purified by flash chromatography (on silica Merck-60, preabsorbed in dichloromethane, eluted with 9:1 petrolether-ethyl acetate)

Sources & evidence

ORD record
ord-d012d0fc8ce44977ae17c78d8c595d8f
Source dataset
uspto-grants-1993_06
Patent number
US05218124

Reaction notes

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